2α-hydroxy-8-oxo-buagarofuran | 1609065-91-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2α-hydroxy-8-oxo-buagarofuran
• 英文别名: (1R,4R,6S,9R)-2-butyl-4-hydroxy-6,10,10-trimethyl-11-oxatricyclo[7.2.1.01,6]dodec-2-en-8-one
• CAS: 1609065-91-9
• 化学式: C₁₈H₂₈O₃
• 分子量: 292.419
• InChiKey: AZQXWDQAQSVNPE-USJZOSNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  AF-5 在 Cunninghamella echinulata AS 3.3402 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以22.8%的产率得到2α,8β-dihydroxy-buagarofuran
  参考文献：
  名称：

  Microbial transformations of buagarofuran, an anti-anxietic agent

  摘要：

  19 structurally diverse metabolites (2-20) were isolated from the transformation of buagarofuran (1), an anxiety agent, by three filamentous fungal strains, Cunninghamella echinulata AS 3.3402, Cunninghamella elegans AS 3.3400, and Absidia coerulea AS 3.3538. Their structures and identified on the basis of extensive spectroscopic data (HRMS, NMR, IR, and CD) and chemical methods. All of the metabolites were oxidized products of 1, and metabolite 20 was also one of mammalian metabolites. Metabolites 8, 10-12, and 20 significantly inhibited [H-3]-NE re-uptake, and 8 and 9 strongly inhibited [H-3]-5-HT re-uptake in the rat brain synaptosomes at 10 mu M in vitro. The structural diversity of the microbial transformed metabolites of buagarofuran in the present report would give a favorable opportunity to probe its mammalian metabolism and better shed light on its pharmacokinetics and pharmacodynamics in vivo. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.011

文献信息

• Microbial transformations of buagarofuran, an anti-anxietic agent
  作者：Lirui Qiao、Chengxue Ji、Dewu Zhang、Lin Yang、Ridao Chen、Jianjun Zhang、Jungui Dai

  DOI：10.1016/j.tet.2014.04.011

  日期：2014.6

  19 structurally diverse metabolites (2-20) were isolated from the transformation of buagarofuran (1), an anxiety agent, by three filamentous fungal strains, Cunninghamella echinulata AS 3.3402, Cunninghamella elegans AS 3.3400, and Absidia coerulea AS 3.3538. Their structures and identified on the basis of extensive spectroscopic data (HRMS, NMR, IR, and CD) and chemical methods. All of the metabolites were oxidized products of 1, and metabolite 20 was also one of mammalian metabolites. Metabolites 8, 10-12, and 20 significantly inhibited [H-3]-NE re-uptake, and 8 and 9 strongly inhibited [H-3]-5-HT re-uptake in the rat brain synaptosomes at 10 mu M in vitro. The structural diversity of the microbial transformed metabolites of buagarofuran in the present report would give a favorable opportunity to probe its mammalian metabolism and better shed light on its pharmacokinetics and pharmacodynamics in vivo. (C) 2014 Elsevier Ltd. All rights reserved.